Homer, say, entertaining English classicist (5)
I believe the answer is:
beard
'classicist' is the definition.
(I know that Beard is a classicist)
'homer say entertaining english' is the wordplay.
'homer say' becomes 'bard' (Homer was an ancient poet or bard).
'entertaining' is an insertion indicator.
'english' becomes 'e' (abbreviation).
'bard' going around 'e' is 'BEARD'.
(Other definitions for beard that I've seen before include "Oppose with effrontery" , "Vandyke, perhaps" , "Hair on the chin" , "Facial hair" , "Facial growth" .)